Bromine → 2-Bromo-1-(4-trimethylsilanylethynylphenyl)propan-1-one

HRID 244383Notes

Reaction equation

HRID 244383 reaction equation
[Br:1]Br.[CH3:3][Si:4]([C:7]#[C:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:11][CH:10]=1)([CH3:6])[CH3:5]>O1CCCC1.O>[Br:1][CH:16]([CH3:17])[C:15]([C:12]1[CH:11]=[CH:10][C:9]([C:8]#[C:7][Si:4]([CH3:5])([CH3:6])[CH3:3])=[CH:14][CH:13]=1)=[O:18]

Participants

5

Reactant 2

HCID 24408BromineHCID 673631271-(4-Trimethylsilanylethynylphenyl)propan-1-one

Product 1

HCID 873708042-Bromo-1-(4-trimethylsilanylethynylphenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Bromine (8.4 g) is slowly added to 1-(4-trimethylsilanylethynylphenyl)propan-1-one (10.0 g) in 100 ml of tetrahydrofuran at 0° C. and subsequently stirred at room temperature for 2 h. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The remainder is purified by chromatography on silica gel, using a mixture of heptane/ethyl acetate 19:1 as eluent to obtain 2-bromo-1-(4-trimethylsilanylethynylphenyl)propan-1-one as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe remainder is purified by chromatography on silica gel
  6. additiona mixture of heptane/ethyl acetate 19:1 as eluent

Sources & evidence

ORD record
ord-63fffd74425d415bb1f4d9b1bcbe6a17
Source dataset
uspto-grants-2014_02
Patent number
US08658644B2

Reaction notes

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